Server 2016 End of Life: Key Dates and Update Challenges

Windows Server 2016 is reaching a critical milestone as it approaches the end of its lifecycle. As the end of support date draws near, it is essential for businesses and IT professionals to understand the implications and take proactive steps to ensure a smooth transition.

LeoMorg: Revolutionizing Data Analysis for Individuals

When Does Windows Server 2016 Support End?

Windows Server 2016’s mainstream support expired on January 11, 2022.  After this date, the server no longer receives some updates, but the security and security updates are still provided through the extended support period, which lasts until January 11, 2027. The end of mainstream support means that Windows Server 2016 no longer receives bug fixes, improvements, or new features.  However, during the extended support period, Microsoft will continue to provide security updates to address critical vulnerabilities and security issues. 

What Happens When Windows Server 2016 Reaches End of Life?

When Windows Server 2016 reaches the end of its extended support on January 11, 2027, it will no longer receive any updates or security patches from Microsoft.  This means that organizations running Windows Server 2016 will face the following challenges:

  1. Server Patching Becoming Problematic: Without regular security updates, keeping Windows Server 2016 systems patched and secure will become increasingly difficult. 
  2. Increased Risk of Cyber Attacks: The lack of security updates leaves Windows Server 2016 systems vulnerable to potential cyber attacks, as new vulnerabilities may be discovered and exploited without the availability of security patches. 
  3. Increased Risk of Security Compliance Issues: Many regulatory bodies and industry standards require the use of supported software. Running Windows Server 2016 after the end of extended support may lead to compliance issues and potential fines or penalties. 

Upgrading to Newer Windows Server Versions

To mitigate the risks associated with the end of Windows Server 2016 support, organizations should consider upgrading to newer, fully supported versions of Windows Server. The two most recent versions are Windows Server 2019 and Windows Server 2022.

Windows Server 2019 vs. Windows Server 2022

When comparing Windows Server 2019 and Windows Server 2022, there are several key factors to consider:

  • Support Timeline: Windows Server 2019 mainstream support ended in January 2024, while Windows Server 2022 mainstream support is expected to continue until October 2026. 
  • Features and Capabilities: Windows Server 2022 offers several improvements over Windows Server 2019, including enhanced security features, improved performance, and support for the latest hardware and software technologies. 

Based on the support timeline and feature enhancements, upgrading to Windows Server 2022 is the recommended path to ensure the longest possible support period and access to the latest capabilities. 

Challenges and Considerations for Upgrading

Upgrading from Windows Server 2016 to a newer version can present several challenges that organizations should be aware of:

  1. Hardware Compatibility: Depending on the age and capabilities of the existing hardware, upgrading to a newer Windows Server version may require hardware replacements or upgrades. This can add significant cost and complexity to the migration process. 
  2. Application Compatibility: Some legacy applications or custom-developed software may not be compatible with newer Windows Server versions, requiring either application updates or the use of compatibility modes. This can complicate the upgrade process and delay the migration timeline. 
  3. User Adoption and Training: Upgrading to a new Windows Server version may require end-user training and change management to ensure a smooth transition and minimize disruptions to daily operations. 
  4. Licensing and Cost: Upgrading to a newer Windows Server version may require the purchase of new licenses, which can be a significant financial investment, especially for organizations with a large server infrastructure. 

Mitigating the Risks of Windows Server 2016 End of Life

To mitigate the risks associated with the end of Windows Server 2016 support, organizations should consider the following strategies:

  1. Start Planning Early: Begin the planning process for upgrading from Windows Server 2016 as soon as possible. This will allow for sufficient time to assess the impact, budget for the necessary changes, and execute the migration with minimal disruption. 
  2. Assess the Current Environment: Conduct a thorough assessment of the existing Windows Server 2016 infrastructure, including hardware, software, and application dependencies. This will help identify any potential compatibility issues or upgrade challenges. 
  3. Explore Cloud Migration Options: Consider migrating workloads to cloud-based platforms, such as Microsoft Azure, which can provide a more modern and scalable infrastructure with built-in security and maintenance features. 
  4. Implement Robust Backup and Disaster Recovery: Ensure that a comprehensive backup and disaster recovery plan is in place to protect critical data and systems in the event of a security breach or other unexpected issues. 
  5. Maintain Vigilance and Monitoring: Even after upgrading to a newer Windows Server version, continue to monitor the environment closely for any security vulnerabilities or compliance concerns, and apply updates and patches in a timely manner. 


In conclusion, the end of Windows Server 2016 support presents both challenges and opportunities for organizations. By understanding the key dates, update requirements, and upgrade considerations, IT professionals can proactively plan and execute a successful migration to a newer, fully supported Windows Server version, ensuring the continued security and reliability of their infrastructure.

ALSO READ: Ausschütter


Q: When does mainstream support for Windows Server 2016 end?
A: Mainstream support for Windows Server 2016 ended on January 11, 2022.

Q: When does extended support for Windows Server 2016 end?
A: Extended support for Windows Server 2016 will end on January 11, 2027.

Q: What happens when Windows Server 2016 reaches end of life?
A: After January 11, 2027, Windows Server 2016 will no longer receive security updates or bug fixes from Microsoft, leaving systems vulnerable to potential attacks.

Q: Should I upgrade to Windows Server 2019 or 2022?
A: Upgrading to Windows Server 2022 is recommended to take advantage of the latest security features and extended support timeline.

Q: What are the key challenges when upgrading from Server 2016?
A: Key challenges include hardware compatibility, application compatibility, user adoption, and licensing costs.

Q: How can I mitigate the risks of Server 2016 end of life?
A: Plan early, assess your environment, explore cloud options, implement robust backups, and maintain vigilance after upgrading.

Leave a Comment